I grew up in penny loafers, so I’ve got an admitted soft spot over here. And yet, there’s something so polished-but-casual about the look, whether pairing your pennies with skirts or trousers, cotton or tweed, black or beyond. My current favorite? This borrowed-from-the-boys version made in Portugal, which boasts comfort and style alike.
BYOP (bring your own pennies), but of course, my 2 cents is always free.
To Buy: Mr. Dickie Loafer ($315) at The Office of Angela Scott